Caldwell was featured on DaBaby’s track “Joggers” from his debut album Baby on Baby in March 2019. He was then featured on Asian Da Brat’s 2019 mixtape Unfuccwitable, on the track “I Love It”.

In May 2019, Caldwell signed with Interscope Records. He then released his debut album under the label, BIG 4X, on May 10, 2019. The album contained guest features from DaBaby, Offset, NLE Choppa, Young Nudy, & Lil Durk. The album peaked at number 50 on the Billboard 200, and received positive reviews.

In the following months, he released singles such as “Tomorrow” featuring Moneybagg Yo, “Flintstones” featuring BannUpPrince, “Boat 4 Vegas” featuring Lil Yachty, “Up The Smoke” with Offset, and “Long.” He revealed the album’s title during an interview with music website Groovy Tracks. In September 2019, he was featured on the track “Really” from DaBaby’s second studio album Kirk. The song debuted and peaked at number 63 on the Billboard Hot 100, making it Caldwell’s first entry on the Hot 100.

On January 17, 2020, Caldwell released his second studio album, Rich Youngin. It included features from DaBaby, Lil Baby, Blac Youngsta, and Offset. It peaked at number 29 on the Billboard 200. The album received lukewarm reviews from critics.

In February 2020, Caldwell earned his first Billboard-charting single as a lead artist and his second charting single overall, with “Go Stupid” debuting and peaking at number 60 on the Billboard Hot 100. On July 27, 2020, Stunna 4 Vegas released a collaboration with DaBaby titled “No Dribble”.